Kilmeade was a freelance sports anchor for WVIT (NBC) in Hartford, beginning in 1997. He was a sideline reporter for the MSG Network, where he covered the New York/New Jersey Metro-Stars, a major league soccer team based in Giants Stadium.

Later, he worked as a feature reporter and anchor for Newsport TV, where he hosted Newsport Journal, a daily magazine show for the national sports network. Additionally, he also anchored Scoreboard Central, a live half-hour general sports program. He has ten years of self-proclaimed experience as a stand-up comedian.[3]

Kilmeade is the author of The Games Do Count: America's Best and Brightest on the Power of Sports[4] and It's How You Play the Game.[5] He is a frequent anchor of The Five airing nightly at 5pm eastern on FNC. In April 2006, he filled in the Fox News Radio time slot of former Fox anchor Tony Snow, who had left the network to become Press Secretary in the George W. Bush Administration.

Kilmeade faced criticism after expressing support for the far-right English Defence League, often described as an extremist group,[8] during an interview with their leader 'Tommy Robinson' (real name Stephen Lennon). He finished the interview with the words "Tommy, we got your back and we'll definitely look to keep in touch, it's great what you're doing".[9]

On July 8, 2009, Kilmeade and two co-hosts were discussing a study that, based on research done in Finland and Sweden, showed people who stay married are less likely to suffer from Alzheimer's disease. Kilmeade commented, "[In the United States] we keep marrying other species and other ethnics...". Ignoring attempts by co-host Gretchen Carlson (who is of Swedish descent) to interrupt him, he added, "See, the problem is the Swedes have pure genes. Because they marry other Swedes .... Finns marry other Finns, so they have a pure society. In America we marry everybody, we marry Italians and Irish."[10]

On July 20, 2009, Kilmeade apologized for his remarks, saying, "I made comments that were offensive to many people. That was not my intention, and looking back at those comments I realize they were inappropriate. For that I sincerely apologize. America [is a] huge melting pot, and that is what makes us such a great country..."[11]

On October 4, 2013, Fox News meteorologist Maria Molina was brought on Fox and Friends to talk about tacos to celebrate National Taco Day. Kilmeade asked Molina: "So what are the tips we need to know? You grew up on tacos, correct?" Molina denied it, explaining she was Nicaraguan and that tacos are not native to Nicaragua. At this point Kilmeade's co-host Elisabeth Hasselbeck asked Molina "But if you did, if you did grow up on tacos?"[18][19]

On June 3, 2014 Kilmeade made a reference about Bowe Bergdahl's father on air stating “I mean, he says he was growing his beard because his son was in captivity. Well, your son’s out now. So if you really don’t want to no longer look like a member of the Taliban, you don’t have to look like a member of the Taliban, are you out of razors?"[20]